On Thursday, March 19, 2015 at 9:22:34 PM UTC-4, trader_4 wrote:
On Thursday, March 19, 2015 at 9:16:40 PM UTC-4, wrote:

Looks like it will be just fine for a while. Weeks, maybe months. I'd
have looked at some sor of flasjing, best installed when the roof was done.

It likely has flashing underneath...but obviously since it leaked something went wrong.

Bingo. Flashing. That repair is a hack job. If the flashing
was properly done, ice daming should not be able to back up water
high enough to go over top of it. And that caulk at the roofline
isn't where the problem is. The problem is something is wrong with
the flashing. If ice daming got water over the flashing, it's going
to get it over the 1/2" height of that caulk too. Where vertical
surfaces meet the roof, flashing is the answer, never caulk.

Here's a diagram of how the step flashing should be done on the raked sided:

http://www.civil.uwaterloo.ca/beg/Dr...of_flash-1.gif

And a pic of it when done:

http://www.nachi.org/images10/1-13-9.jpg

Notice the intentional ~1" gap between where the siding ends and the
roof.


And on the other part, ie the headwall across the top:

http://www.nachi.org/images10/1-14-1.jpg


The above is the way it's done.